Well winamp crashes for me every time.
as far as itunes, i am using it, but I sure as hell dont see 2 window panes to represent my music folder, and that of the ipod, to simply drag and drop these things. Maybe you can elaborate.
So far, I had to add songs to a playlist, then i would highlight the ipod icon, then click "sync". Then i could choose which playlist to add. To me thats a huge fuckaround. Especially, since this chick dont speak english, and my german just aint the best to explain it to her :p.